Jenny Winchester
by LotsofLovely
Summary: A look throughout the seasons as Sam and Dean are joined by Sam's twin sister, Jenny. Sis!fic, starts with S1E1.


"What does it look like?" Jenny asked, propping the phone on her shoulder while she shoved clothes into her duffel bag, "Tell me you sprung for a massive rock."

"_It's big enough. It looks like a ring...what do you want me to say?"_

"You are such a guy." Jenny laughed, "Do you know how you are going to pop the question yet? You can't do something lame-" she paused, glancing at the bathroom door as the shower stopped, "Damn it, Dean's done with his shower, I'll have to call you back later. We'll be hitting the road soon, so it'll probably be late."

"_Okay, I'll keep my phone near. Be safe."_

"Always, Sam. Take care." Jenny responded, her affection for her twin brother clear in her voice.

She slipped the phone in her pocket, and quickly flipped open a book, trying to look innocent and disinterested as Dean opened the bathroom door and walked into the room, toweling his hair dry.

"What's up, Jen?" Dean asked suspiciously, taking in the expression on her face and the book in her hands, "What are you doing?"

"Reading, duh." Jenny retorted, knowing she was busted-she never could lie or keep secrets from either of her brothers, "We're leaving in 10, so try not to spend too long getting ready, Princess."

Dean raised an eyebrow, "Reading, huh?" He walked to his younger sister, taking the book from her hands and turning it around, "It's usually easier when the words are facing the right direction, "So what are you really doing?" He studied her for a moment, then crossed his arms over his chest, "You were talking to Sam."

It was a statement more than a question, and Jenny looked away with a mixture of guilt and anger. Dean had always taken the fight between Sam and their father personally, as an act of betrayal, but Jenny had never wanted to cut Sam off of the family. She missed her twin brother terribly and cherished any contact they could maintain. She wished their Dad and Dean would understand, or at the very least accepted the fact that she was never going to turn her back on any of them. She shrugged slightly, not wanting to fight, and stood, flinging her bag over her shoulder, "He's my brother."

"I'm your brother." Dean replied, his gaze narrowed, "Sam walked out on us, he _left_ us. I can't believe you still call him."

Jenny rolled her eyes; it wasn't the first time they had been over this and she was used to her brother's stubborn disposition when it came to the subject of their brother (or really anything he felt strongly about, stubbornness was a trademark Winchester trait). "Just put your crap in the car and let's get rolling, Dean. We'll never find Dad if we stay here and argue all day."

"Yeah, whatever." Dean muttered, quickly scanning the room to see if there was anything they left behind. In this life, it was important to not leave a speck of evidence behind.

Jenny was waiting for him in the passenger seat when he finally shut the trunk, and he could tell by the look on her face that she wanted to _talk_. He hated that look and had hated it since the twins were in diapers, those stupid puppy dog expressions that both Jenny and Sam had perfectly before they could even walk. He slid into the driver's seat and cut her off before she could even bring the subject up yet again. "No, we're not getting Sam involved in this."

"But Dad could be hurt, or worse. We could use his help."

"Sam doesn't care about Dad, he doesn't care if we need his help. He walked out on us, Jen, what makes you think he'll give a rats ass if Dad's in trouble?" Dean questioned harshly, the direction of the conversation making him incredibly uncomfortable, "I'm not going to drive us all the way to Stanford for him to slam the door in our faces."

"He won't slam the door in our faces," Jenny replied calmly, "Sure, Sam is distant-he hasn't talked to you or Dad in years, but it's not because he hates you. If anything, it's because he's a stubborn ass just like you are. He stayed away because Dad made him feel like that was his only choice. You can't blame him for that, Dad's the one who told him to stay gone."

"He shouldn't have left to begin with."

Jenny exhaled loudly, feeling the beginnings of a headache forming, "He's a big boy, Dean, he is free to make his own choices. And he's doing great for himself, he-"

"I don't want to hear about it." Dean cut her off, "We're not going to Sam, and that's final."

Eighteen hours later, they pulled up in front of Sam's apartment, and despite his initial hesitation, even Dean was starting to feel excited about the prospect of seeing the kid he practically raised and he was only slightly irritated with Jenny for forcing him into the decision. He turned off the ignition and pulled the key out, "Rise and shine, kiddo, we're here."

"I'm up, I'm up." Jenny tiredly answered, rubbing her eyes and opening the car door, "He is going to hate us for barging in at this time of night."

"Less of a chance of him turning us down if he's half-asleep." Dean called over his shoulder as he approached the door, "Toss me your lock-pick."

Dean easily caught the object as it sailed through the air, opening the front door as quietly as possible despite Jenny's quiet mutterings about ringing the bell like a civilized person. He didn't want to make a production out of this and he didn't want Sam to have time to think of a reason to turn them down after they had detoured in this direction, which made a surprise attack the easiest route to take.

He wasn't too surprised when he was attacked by Sam, the dim light showing just enough features to see that his younger brother (still...always…) needed a haircut. Easily defending himself against Sam's attack, he pinned his brother to the ground, "Woah, easy there, Tiger."

"Dean?" Sam's voice clearly showed the surprise he felt at the arrival of his big brother, "What are you doing here?"

"Well, I was looking for a beer-"

"Sam," Jenny interrupted, not wanting to waste time with small talk at this time of night, not when they were here for a reason, "It's Dad."

"Jen!" Sam exclaimed, enveloping his twin in a tight hug, "You're here too."

"Nothing escapes you." Dean deadpanned. Any further response was cut off by the light coming on, which caused him to squint against the sudden change.

"Sam? What's going on?" Jess asked sleepily, standing in the doorway. She realized Sam wasn't alone and a look of shock and worry crossed her face as she asked, "Who are you?"

"Dean, Jen, this is Jess. Jess, this is-"

"_The_ Dean and Jen? Your brother and sister?" Jess asked, her expression quickly turning into one of pleasant surprise, "Sam's told me so much about you!"

Dean eyed Jess with a smirk that definitely looked like he was going to comment on Jess's skimpy pajamas, so Jen quickly cut him off by saying, "Sam, we're here because of Dad. He's been hunting and hasn't been home for awhile."

Sam frowned, torn between wanting to brush it off as typical Dad behavior but still feeling a bit of churning concern at the mention that something may be wrong. He knew that Dean and Jenny wouldn't worry if there wasn't a good reason to-neither were known as alarmists, but the mere mention of his Dad brought up tons of emotions that he had long ago buried and hoped to never re-visit and he wished he didn't have to take all of this in at ungodly-o'clock. It was so much easier to think Dad was on a bender somewhere instead of even considering the possibility that he was hurt or worse.

"Jess, can you excuse us?" Sam asked, his voice trembling ever so slightly. His history with their father was so complicated and messy, it wasn't something that needed to be discussed in front of Jess. Hell, he wished he didn't have to think of his Dad at all.

"What happened?" Sam asked, looking from the brother he had always trusted to have answers to the sister who had earned the spot of being the only one not to turn their backs on him when he left. "Are we sure he's not just...being Dad?"

"It's been weeks." Jen explained, "Dean and I have been retracing his steps, but we're hitting dead end after dead end. We don't know what's going on, but he isn't answering any of his phones and it's like he vanished into thin air."

"Jenny thinks your big college brain could be of some help to us." Dean added, "Will you come?"

Sam looked torn, a frown crossing his tired features, "I...I don't know, guys. I can't just up and leave in the middle of the night. I have a life here."

"Just come with us for a few days." Jenny pleaded, "If we don't make any headway, we'll bring you back in time for class Monday. Please, Sam."

Sam groaned as Jenny pouted, blinking her round eyes in a way that completely prevented him from being able to say no. With a heavy sigh, he relented, "Fine, I'll go pack a bag." He glanced in Dean's direction with a semi-exasperated expression and asked jokingly, "How do you put up with her?"

"Years of practice." Dean replied dryly, though his posture seemed to relax a bit now that Sam had agreed. He didn't realize how much he was hoping his brother would join them until he had committed to making the journey. Suddenly, he felt like nothing could go wrong. It had been years since the three of them had been on a case together, but he still could clearly remember how much better they worked as a team. They each had their own strengths and they complimented each other perfectly.

Jenny could sense the relief Dean was feeling and she was able to relax as well, knowing she had made the right choice by pushing Dean to drive to Stanford, "Laugh it up, boys, you know you'd be miserable without me." she teased, walking to the bookshelf and picking up a picture of Jess and Sam and smiling wistfully at the happy couple (after all, who wouldn't want a relationship like that?) before turning back to her brothers, "Can we skip the part where you pick on me and fast forward to the part where I get to go back to sleep in the car?"

"Depends; do you still drool?" Sam teased with a wink, unable to resist. "Give me five and I'll be ready to go."

True to his word, five minutes later the three of them were walking downstairs, quietly discussing their father and his disappearance.

"I'm just saying, it could be nothing." Sam said defensively, walking shoulder to shoulder with Dean while Jenny lagged behind, more than happy to let her brothers catch up while she followed at a reasonable distance. Sam and Dean had always had a special relationship that she had admired. Jenny was close to both of her brothers, it was a byproduct of being raised in such close quarters, especially in their line of work, but she didn't share the same bond with them that the two boys shared. Jenny and Sam were close, they had a 'twin thing' going on, as their Dad liked to say, and she was closer to Sam than she was to Dean, but even their 'twin thing' couldn't hold a candle to the close bond of her brothers. They had their own way of communicating without words and a sense of trust that seemed unshakable. As a child, Jenny had been jealous of the friendship between her brothers, but now that they were adults, she was able to look past that and just be proud that they hadn't become cold and heartless like so many other hunters tended to become.

"I wouldn't have taken you away from school if it was nothing." Dean retorted, grabbing Sam's bag when they got to the car and throwing it in the trunk, "I know you and Dad haven't always seen eye to eye on things-" he paused while Sam snorted in agreement at the understatement, "but he's Dad-"

"I know, we look out for our family." Sam said heavily, pausing at the passenger door and looking back at Jenny as if to ask which one of them should get the front. Jenny grabbed the handle for the back door, yanking it open with a yawn that she was intentionally over-emphasizing so Sam wouldn't try to be nice or noble or something equally ridiculous when she let him have ride shotgun.

"I'm claiming the whole backseat as my bed." Jenny declared, "You two get to be my chauffeurs."

"Jen-" Sam started to protest, knowing that he was taking her spot, after all, she had been the one who had been hunting alongside Dean for all of this time while he was away.

"I'm tired, Sam." Jenny replied with a reassuring smile, silently communicating that he needed to shut up and get in the damn car. It seemed to work, because he didn't try to offer her the seat again and instead sat down and shut the door.

Dean smirked, turning the key and bringing his Baby to life, "Are you two princesses done yapping?"

ACDC blasted through the speakers and Sam immediately fell into the routine of half-heartedly complaining about the music choice and volume, followed by Dean reminding Sam about the car rules regarding the radio. In the backseat, Jen leaned her head back and closed her eyes, a smile on her face. Finally, things were as they should be.


End file.
